EP2318346A1 - Ethers de polyols et leur procédé de préparation - Google Patents

Ethers de polyols et leur procédé de préparation

Info

Publication number
EP2318346A1
EP2318346A1 EP09791658A EP09791658A EP2318346A1 EP 2318346 A1 EP2318346 A1 EP 2318346A1 EP 09791658 A EP09791658 A EP 09791658A EP 09791658 A EP09791658 A EP 09791658A EP 2318346 A1 EP2318346 A1 EP 2318346A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
polyol
process according
groups
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP09791658A
Other languages
German (de)
English (en)
Other versions
EP2318346B1 (fr
Inventor
Michael L. Tulchinsky
John R. Briggs
Cynthia L. Rand
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Global Technologies LLC
Original Assignee
Dow Global Technologies LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Publication of EP2318346A1 publication Critical patent/EP2318346A1/fr
Application granted granted Critical
Publication of EP2318346B1 publication Critical patent/EP2318346B1/fr
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/13—Saturated ethers containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/13—Saturated ethers containing hydroxy or O-metal groups
    • C07C43/135—Saturated ethers containing hydroxy or O-metal groups having more than one ether bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
    • C07C43/1785—Unsaturated ethers containing hydroxy or O-metal groups having more than one ether bound
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • Preferred carbonyl compounds of formula I include: n-butyraldehyde, methylethylketone, 2-undecanone, n-decanal, 2-methylundecanal, n-valeraldehyde, iso- valeraldehyde, n-hexanal, n-heptanal, 2-ethylhexanal, acetone, methylethylketone, 2- pentanone, 3-pentanone, cinnamaldehyde, levulinic acid, l ⁇ -cyclohexanedicarboxaldehyde, l ⁇ -cyclohexanedicarboxaldehyde, cyclohexanone, and mixtures of two or more thereof.
  • R 3 is H and R 4 and R 5 are independently H or Ci- C 4 alkyl. It is also preferred that m be between 1 and 20, more preferably between 1 and 10. Particularly preferred are compounds where m is 1, 2, 3, 4, 5, or 6.
  • Preferred polyols according to embodiment II-6 are glycerol, sorbitol, mannitol, 2- hydroxymethyl-l,3-propanediol, l,l,l-tris(hydroxymethyl) ethane, trimethylolpropane, pentaerythritol, diglycerol and mixtures thereof.
  • diglycerol is meant a compound selected from the following compounds, or a mixture of two or more thereof:
  • Preferred compounds of formula IE are those in which at least one of R 1 and R 2 is not H. Also preferred are compounds where neither R 1 nor R 2 is H.
  • m is between 1 and 1000, more preferably between 1 and 500, and even more preferably, between 1 and 100. In some embodiments, m is between 1 and 10.
  • Methylethylketone (7.21 g, 9.01 ml, 0.1 mol), glycerol (92.09 g, 73.7 ml, 1 mol), and 10% Pd/C (5 wt %, 0.36 g) are charged to a Parr reactor, purged with nitrogen, heated to 200 0 C with stirring and run at 1000 psi of hydrogen for 7 hrs.
  • Example 23 The reaction in Example 23 is repeated, the reaction mixture is transferred from the Parr reactor to a separatory funnel without filtration and extracted with ether (50 ml x 10).
  • the glycerol phase (96.6 g) containing the catalyst is used for a second hydrogenolysis under identical conditions.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne des nouveaux composés d’éthers de polyols et un procédé pour leur préparation. Le procédé comprend la réaction d’un polyol, d’un composé carbonyle, et d’un atome d’hydrogène en présence d’un catalyseur d’hydrogénation, pour fournir l’éther de polyol. Le rapport molaire du polyol sur le composé carbonyle dans le procédé est supérieur à 5/1.
EP09791658.9A 2008-08-25 2009-08-19 Ethers de polyols et leur procédé de préparation Active EP2318346B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US9153008P 2008-08-25 2008-08-25
PCT/US2009/054277 WO2010027663A1 (fr) 2008-08-25 2009-08-19 Ethers de polyols et leur procédé de préparation

Publications (2)

Publication Number Publication Date
EP2318346A1 true EP2318346A1 (fr) 2011-05-11
EP2318346B1 EP2318346B1 (fr) 2013-11-20

Family

ID=41572508

Family Applications (1)

Application Number Title Priority Date Filing Date
EP09791658.9A Active EP2318346B1 (fr) 2008-08-25 2009-08-19 Ethers de polyols et leur procédé de préparation

Country Status (5)

Country Link
US (1) US8829229B2 (fr)
EP (1) EP2318346B1 (fr)
JP (1) JP5702284B2 (fr)
CN (2) CN102131757A (fr)
WO (1) WO2010027663A1 (fr)

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WO2009032905A1 (fr) 2007-09-04 2009-03-12 Segetis, Inc. Composés cétals à partir de polyols et d'oxocarboxylates
KR101808867B1 (ko) * 2009-06-22 2018-01-18 세게티스, 인코포레이티드. 케탈 화합물 및 이의 용도
WO2011106194A2 (fr) * 2010-02-23 2011-09-01 Dow Global Technologies Llc Procédé de fabrication d'éthers de polyol
AU2011285715B2 (en) 2010-08-03 2016-04-21 Gfbiochemicals Limited Methods for the manufacture of acetals and ketals, and the acetals and ketals produced thereby
CA2747190A1 (fr) 2010-08-30 2012-02-29 Dow Global Technologies Llc Agent de coalescence pour compositions aqueuses
BR112013010073A2 (pt) 2010-11-11 2016-07-05 Segetis Inc adutos de éster polihidróxi cetálico, métodos de fabricação e seus usos
US9212176B2 (en) 2010-11-11 2015-12-15 Segetis, Inc. Polyketal adducts, methods of manufacture and uses thereof
US8507718B2 (en) 2010-11-11 2013-08-13 Segetis, Inc. Ketocarboxylic acids, methods of manufacture and uses thereof
WO2012071149A2 (fr) * 2010-11-23 2012-05-31 Dow Global Technologies Llc Agents tensio-actifs alcoxylates d'alcools secondaires ramifiés et leur procédé de fabrication
FR2969146B1 (fr) 2010-12-17 2013-01-11 Fonds De Dev Des Filieres Des Oleagineux Et Proteagineux Fidop Procede de preparation d'ether de polyol
CN107011291A (zh) * 2011-04-26 2017-08-04 陶氏环球技术有限责任公司 来源于糖醇的可再生表面活性剂
US8829206B2 (en) 2011-06-24 2014-09-09 Eastman Chemical Company Production of cyclic acetals or ketals using solid acid catalysts
US9388105B2 (en) 2011-06-24 2016-07-12 Eastman Chemical Company Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals
US8829207B2 (en) 2011-06-24 2014-09-09 Eastman Chemical Company Production of cyclic acetals by reactive distillation
US9056313B2 (en) 2011-06-24 2015-06-16 Eastman Chemical Company Catalysts for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US8785697B2 (en) 2011-06-24 2014-07-22 Eastman Chemical Company Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9000229B2 (en) 2011-06-24 2015-04-07 Eastman Chemical Company Production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US8969598B2 (en) 2011-06-24 2015-03-03 Eastman Chemical Company Production of cyclic acetals or ketals using liquid-phase acid catalysts
AU2013341527B2 (en) * 2012-11-08 2017-05-18 Dow Global Technologies Llc Liquid 1,3/1,4-alkoxylated cyclohexanedimethanol based diacrylates
EP2807925A1 (fr) * 2013-05-26 2014-12-03 Symrise AG Compositions antimcrobielles
JP6536587B2 (ja) * 2014-09-29 2019-07-03 三菱瓦斯化学株式会社 ポリエーテルジオール及びその製造方法
JP6503959B2 (ja) * 2015-07-24 2019-04-24 三菱瓦斯化学株式会社 ポリエーテルジオール及びその製造方法。
EP3601489B1 (fr) 2017-03-22 2023-08-02 SABIC Global Technologies B.V. Additifs pour carburant relevant l'indice d'octane
CN111050571A (zh) 2018-03-16 2020-04-21 陶氏环球技术有限责任公司 泡沫控制
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Also Published As

Publication number Publication date
US20100048940A1 (en) 2010-02-25
CN102131757A (zh) 2011-07-20
WO2010027663A1 (fr) 2010-03-11
JP5702284B2 (ja) 2015-04-15
JP2012500849A (ja) 2012-01-12
EP2318346B1 (fr) 2013-11-20
US8829229B2 (en) 2014-09-09
CN107082742A (zh) 2017-08-22

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